Old School with Shilo Brooks
Old School with Shilo Brooks is a podcast from The Free Press that encourages reading great books. Host Shilo Brooks engages in intimate conversations with fascinating men, from fitness gurus to philosophers, about the books that shaped their lives. The show aims to help listeners become stronger, better men through literature. New episodes are released every Thursday.
Episodes
What ‘The Future Is Female’ Has Meant for Men
For decades, the fight for gender equality has squarely focused on lifting women up—in the workplace, politics, and beyond.
But according to Richard Reeves, president of the American Institute for Boys and Men, it’s the men who now need support.
From childhood, boys are falling behind in school. Men are trailing women in college completion by an even wider margin than existed (in the opposite d
Walter Isaacson on the Sentence That Created America
If America has a mission statement, it is this:
“We hold these truths to be self-evident, that all men are created equal, that they are endowed by their Creator with certain unalienable Rights, that among these are Life, Liberty and the pursuit of Happiness.”
In a special conversation recorded at the George W. Bush Presidential Center, acclaimed biographer Walter Isaacson discusses his new bo
The WWII Novel That Explains America
In this special episode, Shilo Brooks is joined by Pulitzer Prize–winning historian Jon Meacham at the Jack Miller Center’s annual summit on civic education.
They took the stage at the National Constitution Center in Philadelphia, the perfect setting for a discussion about one of Meacham’s favorite books: The Winds of War. Written by Herman Wouk and published in 1971, The Winds of War is an epic
Agatha Christie and the Kidnapping That Inspired Her Greatest Mystery
In this episode, Shilo sits down with veteran journalist Joe Nocera for a deep dive into the world’s best-selling novelist, Agatha Christie.
Nocera’s new investigative podcast is all about the Charles Lindbergh, Jr., kidnapping, one of history’s most infamous crimes, and a key inspiration behind Christie’s Murder on the Orient Express.
They dig into why mystery fiction matters so deeply, the p
Inside the Supreme Court with Amy Coney Barrett
In this special episode, taped live at the George W. Bush Presidential Center, Shilo sits down with Supreme Court Justice Amy Coney Barrett for a wide-ranging interview on the law.
They discuss Barrett’s lifelong love of reading, her tumultuous confirmation process, the Constitution and what it should take to amend it, how she approaches cases where her interpretation of the law differs from her
A New Series From The Free Press | The Lindbergh Conspiracies
Hi Old School listeners! Veteran reporter Joe Nocera has launched a six part series about the Lindbergh kidnapping. Enjoy episode one here and then head on over to The Lindbergh Conspiracies feed for the rest of the season. Joe will be joining me next week to discuss Agatha Christie and how she was inspired by this very case.
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EP01 | The Broken Window
One night in March 1932, the infant s
Roald Dahl: Genius and Bigot
For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.
Roald Dahl gave the world Matilda, James and the Giant Peach, and Charlie and the Chocolate Factory. He was also a vicious antisemite.
A Broadway play about Dahl’s legacy; the new Michael Jackson biopic; Kanye West’s attempted redemption arc; all of these have the
How Sports Became Our Civic Religion
For tickets to our live recording with Jon Meacham in Philadelphia, click here and register. Use code TFP for a 20 percent discount.
In this episode, Shilo sits down with sportswriter Wright Thompson to explore what the ESPN mainstay has learned from decades of covering elite athletes such as Tiger Woods and Michael Jordan. Does greatness require rage, dysfunction, or “daddy issues”? And what do
The Ancient Jewish Wisdom Behind a $5 Billion Company
For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.
As he built Kind Snacks into a $5 billion company, ‘Shark Tank’s Daniel Lubetzky didn’t turn to startup gurus or business manuals—but to a 2,000-year-old Jewish text.
After the death of his father, a Holocaust survivor with whom he was deeply close, Daniel’s rabbi
Neal Stephenson on AI, Rome, and How Civilizations Decline
Neal Stephenson, the prophetic author of cyberpunk classics like Snow Crash and The Diamond Age, has shaped how we imagine the future, from the metaverse to crypto to AI. His science fiction has a way of becoming reality.
But Stephenson’s thinking is just as rooted in the past, returning to timeless questions of empire and decline. In this episode, he joins Shilo to discuss Edward Gibbon’s The Hi
The Two Types of People Who Never Find Happiness
For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.
Life is short. How do we live it well?
Harvard professor Arthur Brooks has spent years studying happiness. In this episode, he joins Shilo to explore what neuroscience, faith, and philosophy reveal about how to live a happy life.
Most of us are caught up in eithe
Hunting Humans for Sport
For tickets to our live recording with Jon Meacham in Philadelphia, CLICK HERE and register. Use code TFP for a 20 percent discount.
Richard Connell’s 1924 short story “The Most Dangerous Game” tells of a hyper-sophisticated aristocrat who hunts human beings for sport on his private island.
In this episode, best-selling author, screenwriter, and former Navy SEAL sniper Jack Carr joins Shilo to
Joan Didion Knew What Hollywood Would Become
The perfect book to read around the Oscars this weekend? Joan Didion’s Play It as It Lays.
In this episode, Shilo sits down with Peter Savodnik to discuss Didion’s 1970 novel—a book that seemed to anticipate everything ugly about Hollywood, celebrity culture, and the spiritual emptiness that we now take for granted on the red carpet and on social media.
They break down why Didion’s story of an a
The NYC Public Defender Who Sends Books to Prisoners
In this episode, Shilo Brooks sits down with New York City public defender Ben Schatz to discuss the novel True Grit–and the nature of justice in America.
Ben founded the nonprofit Books Beyond Bars, which sends requested books (not just random donations) to individuals locked in in New York jails and prisons, giving them dignity, mental escape, and intellectual stimulation.
After discussing
‘The Brothers Karamazov’ Helped Inspire the Catholic App Hallow
Alex Jones was using apps like Headspace and Calm to quiet his mind, but he had fallen away from his Catholic faith. Then he read The Brothers Karamazov, and everything changed.
Alex, who went on to recommit himself to Christ and start Hallow, the Catholic prayer app with millions of users worldwide, believes Dostoevsky’s classic is the perfect book to read for Lent.
In this conversation, Alex
‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic
One particular novel is all over the Epstein files: Vladimir Nabokov’s Lolita. Reportedly, this was the one and only book Jeffrey Epstein kept at his bedside table. He owned a first edition. It pops up in emails and in photos, released by the House Oversight Committee, that show young women with quotes from the book written on their bodies.
Lolita is about a 38-year-old man who kidnaps and serial
The Secret Lives of Ordinary People
Dylan Thomas is one of the 20th century’s legendary poets.
In this episode, English journalist David Aaronovitch joins Shilo to discuss Thomas’ 1954 play Under Milk Wood, a portrait of a small Welsh seaside town, originally produced for radio.
With rich, musical language, Thomas reveals the secret interior lives of the villagers—their dreams, lusts, resentments, and longings—without condescens
David Mamet vs. the Snobs
Pulitzer Prize–winning playwright David Mamet spent his childhood cutting class and reading at the local library. His first pick was Sinclair Lewis’s Main Street, which he pulled off the shelves at just 11 years old.
Decades later, David thinks the book is terrible, its author “a horrible writer,” and its heroine an insufferable busybody. In this episode, Shilo pushes back, defending the novel a
Colin Quinn on Incels, Woke Activists, and Peaking at 14
In this episode, legendary comic Colin Quinn dives into a cult classic that still makes him cry with laughter: John Kennedy Toole’s A Confederacy of Dunces.
The novel follows the misadventures of an overweight, pretentious misanthrope still living with his mother in 1960s New Orleans. It’s a book that turns fart jokes into high art. It’s also, somehow, a love story between a fat incel and a woke
Dante: The Most Famous, Least Read Poet
Dante Alighieri is one of the most consequential poets in human history, and his The Divine Comedy is essential to understanding Western civilization itself. And yet, though most of us have heard of Inferno, Dante remains one of the least read of all the greats. His masterpiece unfolds in three parts—Inferno, Purgatorio, and Paradiso—charting a journey from despair to redemption.
For literature
America’s Most Righteous War Produced Its Best Anti-War Novel
In Venezuela, a U.S. operation that captured President Nicolás Maduro has sent shock waves through the hemisphere. In Iran, a deadly crackdown on nationwide protests has Washington threatening the possibility of direct military action. Meanwhile, war rages on from Ukraine to Sudan. All this instability and conflict makes now a good time to revisit the most acclaimed anti-war novel in American hist
Why ‘Middlemarch’ Changed This Catholic Priest’s Life
Middlemarch is George Eliot’s (real name Mary Ann Evans) masterpiece. The 900-page Victorian novel is about the people living in a fictional English town in a time of enormous changes.
In this episode, Shilo Brooks sits down with Dominican friar Father Jonah Teller to discuss what makes the book worth reading. Their conversation tackles the novel’s major themes: marriage in all its mismatched f
The Lost Art of Taking the Piss with Richard Dawkins
Richard Dawkins is best known as a formidable evolutionary biologist and biting critic of religion. But when he wants a break from polemics and proofs, he turns to P.G. Wodehouse for a belly laugh.
Wodehouse’s satire skewered British aristocrats, Hollywood phonies, and self-important moralists with surgical precision. In this episode, Shilo Brooks sits down with Dawkins to find out why the Briti
Living Through the Fall of a Regime
“If we want things to stay as they are, things will have to change.” This famous line from The Leopard has become a shorthand for moments when a ruling order senses its own looming downfall.
And it feels eerily relevant now, in an age when the liberal order we cherish seems increasingly unsteady. We are living in a moment when we shout “regime decline” from the rooftops. Giuseppe Tomasi di Lampe
Read This Book Instead of ‘The Catcher in the Rye’
According to Ryan Holiday, Walker Percy’s The Moviegoer is like the better, more mature cousin to The Catcher in the Rye. In this episode, Shilo Brooks sits down with the author and Daily Stoic founder to discuss the quiet Southern novel set in postwar New Orleans.
The book follows a Korean War veteran who has money, women, and a respectable job but whose inner life is defined by existential mal
George Orwell’s Lessons on the Class Divide
Most of us have read 1984 or Animal Farm. But fewer know of George Orwell’s first great work—an unvarnished account of his descent into the world of society’s outcasts. In this episode of Old School, Shilo Brooks sits down with Rob Henderson to discuss Down and Out in Paris and London, which is inspired by Orwell’s real-life plunge into the slums of two great European cities.
Henderson draws on h
What ‘The Great Gatsby’ Taught Fareed Zakaria About America
It’s been 100 years since The Great Gatsby was published. In this episode, Shilo Brooks sits down with journalist Fareed Zakaria to explore why the F. Scott Fitzgerald novel still feels so modern.
Zakaria shares his experience discovering the classic as an Indian immigrant, describing Gatsby as his gateway to understanding America. Together, they unpack the book’s enduring themes: the allure of
How Thomas Sowell Transformed Coleman Hughes
Why do we believe what we believe? And how do those beliefs shape our politics?
Thomas Sowell, one of the world’s most influential economists and social philosophers, set out to answer this question in his 1987 book, A Conflict of Visions. In it, he traces the underlying logic behind all modern political divides—why it is that knowing someone’s position on one issue, say gun control, makes it ea
Nick Cave on ‘The Adventures of Pinocchio’
Carlo Collodi’s The Adventures of Pinocchio is a dark, dazzling Italian fable that is worlds apart from Disney’s sanitized version. Beneath its fantasticism and humor, the story is brimming with poverty, violence, and existential peril. In this episode, Australian rock legend Nick Cave joins Shilo Brooks to talk about one of the best-selling and most widely translated books ever written.
Toget
Why We Still Need Plato
What is justice? And why should we live justly? These questions lie at the heart of Plato’s Republic, the foundational text of Western philosophy. In building his utopian city, Plato reveals how the quest for perfect justice can slip into tyranny. Yet his call for relentless self-examination—for resisting nihilism and seeking meaning—remains a starting point for us all.
In this episode, Dr. Corne
What Steven Pinker Taught this Pro Bodybuilder about Genetics
Dr. Mike Israetel is a bodybuilder and scientist who believes reading is as important as a gym session. Steven Pinker’s The Blank Slate changed his life. In this episode, Israetel joins Shilo Brooks to discuss how this explosive book on genetics, human nature, and the myth of infinite potential turned his own outlook (and coaching style) upside down, inspiring humility, killing illusions, and shar
MeatEater’s Steven Rinella on Lessons from the Wilderness
Few people have turned a love of the wild into a cultural force quite like Steve Rinella, the outdoorsman and author behind the MeatEater empire. Jim Harrison’s Wolf, published in 1971, changed Rinella’s life. In this episode, Rinella sits down with Shilo Brooks to discuss this stream-of-consciousness novel replete with chaos and male angst. He reflects on growing up in rural Michigan and seeing h
The Old Man and the Sea with Admiral James Stavridis
Admiral James Stavridis once commanded fleets as Supreme Allied Commander of NATO. Now he commands a collection of 5,000 rare books. Ernest Hemingway’s The Old Man and the Sea changed Stavridis’ life. In this episode, the admiral sits down with Shilo Brooks to discuss the themes of hardship, pride, and resilience that appear in Santiago’s epic struggle at sea. Stavridis, who stuck out in the milit
Introducing: Old School with Shilo Brooks
Fewer of us than ever are reading books for pleasure. Shilo Brooks is on a mission to change that. Old School is a new podcast from The Free Press about great books and how reading them can make us stronger, better men. The show features intimate conversations with fascinating men—from fitness gurus to philosophers—about the books that shaped their lives. Coming October 9th.
Learn more about yo
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